Sodium Carbonate → 1-(3,4-Dimethoxyphenyl)ethanol
Reaktionsgleichung
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ru+2].[Fe]>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]Komponenten
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
Tris(triphenylphosphine)ruthenium(II) chloride (0.38 mg, 0.4 μmol, 0.1 mol %) and a chiral ligand (M=Fe, R=t-Bu, Ar=C6H5—, 0.26 μmol, 0.065 mol %) were dissolved in toluene (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 120° C. After the mixture was cooled to room temperature, 3,4-dimethoxyacetophenone (0.4 mmol), toluene (2 mL) and an aqueous solution of sodium carbonate (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (10 atm) at 25° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5). Accordingly, pure 1-(3,4-dimethoxyphenyl)ethanol was obtained and the ee value (ee=96%) was measured by GC analysis.
Aufarbeitung
- temperatureheated
- temperatureAfter the mixture was cooled to room temperature
- stirringstirred for 24 h under H2 (10 atm) at 25° C
- customThe solvent was removed under reduced pressure
- customthe resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5)
Quellen und Nachweise
- ORD-Eintrag
- ord-7e3c47d2d0d34f0fa0339c1be3948d90
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08962852B2
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